Base Catalyzed Abnormal [3 + 2]-Cycloaddition between Isatin <i>N</i>,<i>N</i>′-Cyclic Azomethine Imine 1,3-Dipole and 3-Methyleneoxindole for the One-Step Construction of Tetracyclic Bispirooxindoles
Xiang‐Jia Song, Hong‐Xia Ren, Min Xiang, Chenyi Li, Fang Tian, Li-Xin Wang
Abstract
An abnormal [3 + 2]-cycloaddition and highly effective and convenient one-step preparation of tetracyclic bispirooxindoles containing two all-carbon quaternary spirocenters from isatin N,N′-cyclic azomethine imine 1,3-dipole and 3-methyleneoxindole in the presence of catalytic organic base has been disclosed. A variety of bispirooxindoles bearing a dinitrogen heterocycle with four adjacent cycles have been obtained in excellent yields (up to 95%) and diastereoselectivities (>99:1) under mild conditions.
Topics & Concepts
IsatinChemistryImineCycloadditionCatalysisAzomethine ylideSchiff base1,3-Dipolar cycloadditionBase (topology)Organic baseMedicinal chemistryCombinatorial chemistryOrganic chemistryStereochemistryMathematical analysisMathematicsAsymmetric Synthesis and CatalysisSynthesis and Catalytic ReactionsBioactive Compounds and Antitumor Agents